I skated street in the nineties (still do, shout-out to /r/OldSkaters) and have made that connection too. But I am chaotic good aligned so I was more into the building/tinkering side. So more "how can I repurpose this piece of trash to something skatable" rather than "how/when can I arrange stuff so I can skate this unexpected sculpture". I think this is more like hacking in the modern sense of coding/scripting just to create stuff for your own use.
In my case we are talking the second half of the 2000's. Mind you, I was significantly more interested in the skating from the late 90's and what was "modern" back then didn't have much appeal to me. I mean even the photo on that deck is from 1999 iirc and I can still hear the music from the video in my head every time I look at it. I really can't express how happy I was to get my hands on a limited edition deck, signed by both my favorite skater and the photographer.
Pretty impressive you are still doing it 20+ years later. I didn't want to stop but certain life events came into play and eventually it just became one of those things I used to do. For multiple reasons I have no intention of getting back into it but I will admit, I am somewhat curious to give it a try once and see if there is anything left in me.
For me, finding time to keep doing it, despite life throwing curve balls, is what keeps me from getting stuck in the nostalgia of it. So just beware that your nostalgia isn't keeping you from picking it up again. Because it wont be the same when you can't risk breaking an arm because of responsibilities, but it's still fun, just different.
It's awesome that you managed to keep going. For me it was a combination of my best friend from childhood passing away, a heartbreaker and ultimately moving back home in the other side of Europe in the beginning of winter, having to look for a job, sort out a roof over my head(and a ton of other crap) and by the time that had settled and snow had gone away, I was completely out of it. Though I'm still mildly interested in it. Old habits die hard I guess...
